Sodium Hydroxide → HCID 68432135, compound

HRID 2092099Notes

Reaction equation

HRID 2092099 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[O:11])[N:5]=[C:4]([N+:20]([O-])=O)[C:3]=1[NH:23][C@@H:24]1[CH2:29][C@@H:28]2[CH2:30][C@@H:26]([C:27]2([CH3:32])[CH3:31])[C@H:25]1[CH3:33].O.O.[Sn](Cl)Cl.[OH-].[Na+]>C(OCC)(=O)C>[NH2:20][C:4]1[C:3]([NH:23][C@@H:24]2[CH2:29][C@@H:28]3[CH2:30][C@@H:26]([C:27]3([CH3:31])[CH3:32])[C@H:25]2[CH3:33])=[C:2]([Br:1])[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=2)=[O:11])[N:5]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 68432095HCID 68432095, compound

Product 1

HCID 68432135HCID 68432135, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-[5-Bromo-3-nitro-6-oxo-4-{[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]amino}pyridazin-1(6H)-yl]-N-(pyridin-4-ylmethyl)acetamide (32 mg, 0.0616 mmol) in ethyl acetate (3 mL) was stirred with tin (II) chloride dihydrate (72 mg, 0.319 mmol) at room temperature for 2 hours. After completion of the reaction, the reaction solution was basified to pH 9-10 with aqueous sodium hydroxide and filtered through celite. The filtrate was extracted with ethyl acetate, and the extract was dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform/methanol=6/1) to give the desired product (13 mg, 43% yield).

Workup

  1. customAfter completion of the reaction
  2. filtrationfiltered through celite
  3. extractionThe filtrate was extracted with ethyl acetate
  4. dry with materialthe extract was dried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (chloroform/methanol=6/1)

Sources & evidence

ORD record
ord-67b7c751622345ed9b766efe743b5026
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

Loading…